Dimethylamine → dimethylaminotriethylsilane

HRID 745338Notes

Reaction equation

HRID 745338 reaction equation
[CH2:1]([Si:3]([CH2:7][CH3:8])([CH2:5][CH3:6])Cl)[CH3:2].[CH3:9][NH:10][CH3:11]>C(OCC)C>[CH3:9][N:10]([Si:3]([CH2:7][CH3:8])([CH2:5][CH3:6])[CH2:1][CH3:2])[CH3:11]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 13819Chlorotriethylsilane

Product 1

HCID 2758524dimethylaminotriethylsilane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethylchlorosilane, 75.4 g (0.5 mole), was added dropwise to a solution of 73 ml (1.1 mole) of dimethylamine in 500 ml diethyl ether at 10°-20°. A precipitate was removed by filtration, and the resulting filtrate distilled to provide 64.8 g of dimethylaminotriethylsilane as a colorless liquid, bp 88° (46 mm). A 47.8 g (0.3 mole) sample of the silane was added dropwise to a solution of 5 ml (0.09 mole) of sulfur tetrafluoride in 100 ml of ether cooled to -70°. The resulting mixture was allowed to warm to about 23° and stirred for one week. The resulting white solid precipitate was collected on a filter, washed with ether, and dried under nitrogen to give 6.8 g of tris(dimethylamino)sulfonium bifluoride as colorless crystals: mp 117°-120°; 19F NMR (CD3CN) δ-150.4 ppm; 1H NMR (CD3CN) δ+2.95 ppm.

Workup

  1. customA precipitate was removed by filtration
  2. distillationthe resulting filtrate distilled

Sources & evidence

ORD record
ord-4470474f81b748cab2cb36557206379e
Source dataset
uspto-grants-1986_07
Patent number
US04598161

Reaction notes

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